Architecture that guides the freeform drawing of objects by a user to enable the user to produce improved drawings without significant training. As the user draws, the architecture dynamically updates a relevant shadow image proximate (e.g., underlying) the user's strokes. The strokes overlay an evolving shadow image, which shadow image is suggestive of object contours that guide the user during the drawing process. Relevant edge images selected from a large database are automatically blended to construct the shadow image. As the user draws, the strokes are dynamically analyzed using an encoding of overlapping windows for fast matching with the database of images. A top ranked set of matching database edge images are aligned to the drawing, a set of spatially varying weights blend the edge images into the shadow image, and a scoring technique is employed to select the optimum shadow image for display.